hiker in Scotland


Highlands and Islands of Scotland

Hiking the Glens, the Outer Hebrides, and the Isle of Skye

Highlands and Islands of Scotland route-map

Trip Details at-a-Glance

Cost From: $6095  
Length: 10 days
Arrive: Inverness, Scotland
Depart: Inverness, Scotland
Lodging: 9 nights in hotels and historic inns
Meals: All meals included except 2 dinners
Activity: Hiking / Trekking
Trip Level: 9 hiking days on moderate to steep trails, 3-8 hours a day, van support


  • Mysterious Loch Ness, beautiful Glen Affric, historic Glencoe and Inverness
  • Hikes in the spectacular Outer Hebrides and the Isle of Skye
  • Gaelic legends, heather-covered hills, dramatic seascapes
  • Magnificent prehistoric Standing Stones of Callanish
  • Accommodations including two magnificent country estates

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Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.

Special Offer!

$400 discount per person
May 31-Jun 9, 2014 departure

Limit 4 people, new sign-ups only. Please note that these special offers cannot be combined with other discounts.

A sensational meeting of mountain and sea occurs in northwest Scotland, land of mist-shrouded crags, heathered moorlands, brooding castles, and rich legends. We discover the stunning beauty of Scotland the best way—with hikes on age-old trails rising above silver lochans (small lakes), across mountain-ringed glens, and on island paths amid the wild seascapes of the Outer Hebrides. The breathtaking Isle of Skye, the fjord-like inlets of the “far Cuillins,” historic Glencoe, and the splendid sandy beaches of Harris, with its famous weavers, are all on this fantastic journey. Along the way, we drop by a pub or two for a wee dram of whisky, sample fresh scallops and salmon, and discover the proud Gaelic heritage and warm welcome of the Scots.

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-2
Loch Ness / Glen Affric

On our hike along Loch Ness, we’ll keep an eye out for “Nessie,” then discover the trails of Glen Affric, Scotland’s most beautiful glen, with its shimmering lochs and ancient Caledonian pinewoods. Our hotel, the Coul House, is a stone-built 18th century estate secluded in the hills above the small village of Contin.

Days 3-5
Outer Hebrides / Harris and Lewis / Callanish Standing Stones

The Outer Hebrides are one of Scotland's best-kept secrets for walking and hiking. We hike on the Isle of Lewis amid cliffs, seabird rookeries, and iconic lighthouses, then take in the magical setting of the Callanish Standing Stones, a remote megalithic site bathed in legend. On the adjoining Isle of Harris, with its aquamarine bays and boulder-strewn slopes, our hike crosses the dazzling white sands of Huisinis Bay and we visit a Harris tweed weaver to learn about this ancient Hebrides tradition.

Days 6-7
Isle of Skye / Cuillins

Traveling “over the sea to Skye” brings us to the storied isle to which Bonnie Prince Charlie escaped in 1746. We hike among the mysterious rock spires of the Quiraing, convoluted Jurassic landscape has a supernatural quality, and in the brooding Black Cuillins. At a traditional distillery on the shores of Loch Harport with dramatic views of the Cuillins, we’ll try a taste of the sweet, full-bodied single malt whisky made on this renowned island.

Days 8-10

After stopping for a look around photogenic Eilean Donan Castle, which has appeared in many films due to its striking situation on a tidal island, we stretch our legs on a  hike through the narrow Ben Nevis Gorge to one of the highest waterfalls in Scotland. The next day, a fantastically scenic hike brings us into historic Glencoe, perhaps the most dramatic of all of Scotland’s glens, its spectacular scenery a match for its dark history, with overnights in a historic 19th century mansion surrounded by woodland and sea lochs. Depart via Inverness on Day 10.

For a more complete description, Download Full Detailed Itinerary

What the Trip is Like

This trip is rated Level 3+, Moderate to Strenuous. We hike from 3 to 5 hours on most days (with one longer day in Glen Affric) over rolling hills with some steep sections. Distances are not long, but trip members should be in good shape and have good hiking boots. While many of the hikes follow recognized trails, these are not “groomed” trails so they can feel quite rugged, often with muddy sections and loose rocks (but no scrambling required). As is common in Scotland, we may even hike off-trail where the terrain allows. Many hikers prefer to use trekking poles on the less-groomed sections. Most hikes feature an elevation gain of up to 1,000 feet, so a reasonable level of fitness will make the experience more enjoyable. Most of our vehicle transfers to and from trailheads and between destinations are less than an hour. There are longer transfers on Day 5, when we explore West Lewis (up to 90 minutes), on Day 8 when we travel from Skye to Glen Coe (3 hours), and on Day 10 when we transfer back to Inverness (2 hours).  Driving and hiking times are noted, but on first departures, and with full groups, these can vary, sometimes dramatically, from the anticipated times. Road conditions and the group’s level of fitness also affect the travel and hiking times.

A Weather Note: Scottish weather has a fickle reputation and it’s certainly possible to encounter rain and quite strong winds when hiking, even in summer. However, the weather changes quickly, making “sunshine and showers” a common forecast. These climatic conditions give the mountains great atmosphere and can add to the overall experience. They do, however, mean that you need to bring good raingear, including a fully waterproof jacket and waterproof overpants. Note that waterproof ponchos are NOT recommended for hiking in Scotland, as the wind makes them less efficient.

Explanation of Trip Levels


Departures & Leaders

May 31-Jun 9, 2014  Skye McDonald
Jul 12-21, 2014  Skye McDonald

Trip Cost

Prices are for 2014
$6095 (11-14 members)
$6495 (6-10 members)
Single supplement: $590
Forced single supplement: $390
more on pricing

Trip Cost Includes:

  • Expert leadership of a Wilderness Travel Trip Leader and local guides
  • Accommodations in hotels
  • All meals included except 2 dinners
  • Airport transfer on Day 10
  • Land transportation as noted, including ferry travel
  • Entrance fees to several museums, castles, distilleries, and historic sites as per the itinerary

Trip Cost Does Not Include:

International airfare, arrival airport transfer, any meals not specified after each itinerary day, alcohol at meals, airport departure taxes, optional tipping or gratuities to leaders or staff, additional hotel nights that may be necessitated by airline schedule changes or other factors; pre-trip expenses of medical immunizations (if any), travel insurance, or passports and visas; and other expenses of a personal nature (alcoholic beverages, laundry, etc.).

Trip Payment Schedule

At time of reservation: $500
120 days prior to departure: 20%
60 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

Minimum fee: None per person
46-90 days prior to departure: 25% of trip cost
45 days or less: 100% of trip cost

Coul House Hotel

Coul House Hotel

Days 1 to 2 (2 nights), Contin, Scotland

This warmly welcoming hotel is set in beautiful old gardens and brings with it the atmosphere of a traditional Scottish country house. The owner and ...
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Harris Hotel

Harris Hotel

Days 3 to 5 (3 nights), Isle of Harris, Scotland

This family-run hotel is centrally located on the Isle of Harris just two minutes from the ferry terminal. The hotel has a lovely dining room and ...
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Bosville Hotel

Bosville Hotel

Days 6 to 7 (2 nights), Portree, Scotland

The Bosville is a simple family-run hotel that offers a wonderfully warm welcome. Its location is superb, just a couple of minutes walk from both ...
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Glencoe House

Glencoe House

Days 8 to 9 (2 nights), Glencoe, Scotland

The unique Glencoe House, set amid some of Scotland’s most spectacular scenery, accommodates guests in large and beautifully furnished suites. ...
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Note: Listed above are our signature accommodations for this trip. Although it is highly unlikely, we may make substitutions when necessary.

Skye McDonald

Skye McDonald was  born and raised in Scotland in a small village called Scone, the ancient crowning place of the kings and queens of Scotland. After studying agriculture at Aberdeen University, she worked as a  volunteer in Tanzania for two years. Her passion is exploring remote and wild places, and she adores both the mountains and the desert.  “Bringing understanding between peoples of very different cultures and backgrounds is one of the joys of being a Trip Leader, and of course, the chance to make friends around the world.” She has traveled extensively, from the Pindos in Northern Greece to the wadis of Jordan, and she has a special affinity for West Africa, with its diversity of welcoming peoples and wonderful scenery. Closer to home, she delights in sharing the glories of  her native Scotland, and says that a good day scaling some of the beautiful Scottish mountains is hard to beat. Skye speaks German, French, and a bit of Swahili picked up during her years in Tanzania.


WT Trip Leader Skye McDonald is coming home to Scotland to lead our new hiking adventure! Check out this video post Skye sent as she scouted the trails and a lovely Georgian-era home that will be our accommodation in Glen Coe—but remember, her scout took place in the wintry days of December. We’ll be there in the long days of summer! Enjoy this peek, and join Skye to hike with us in Scotland!

Upcoming Trips:

Highlands and Islands of Scotland, May 31-June 9, 2014
Highlands and Islands of Scotland, July 12-21, 2014
England Coast to Coast, July 27-August 9, 2014
England Coast to Coast, August 24-September 6, 2014

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Client Testimonials:

I cannot praise Skye enough. She combined efficiency with attention to individual needs. She’s also very knowledgeable about West Africa. Caroline M., Princeton NJ
Timbuktu & Dogon Country
Skye was one of the best leaders of any trip I have taken, period. Betty G., Boca Grande FL
Timbuktu & Dogon Country
Skye was a first-rate leader in every respect. She made the trip a great experience. Helen D., Petaluma CA
Timbuktu & Dogon Country
Skye was fantastic in every way. Her joy in relating to the local people was a pleasure to watch. Susan R., Old Greenwich CT
Timbuktu & Dogon Country
Skye was off the charts tops. She has a captivating storytelling ability and a sharp wit. We always felt in good hands with her. Kate F., Santa Monica, CA
England Coast to Coast
Skye is a fabulous people person and had the gift of bringing the group together. Linda H., Laguna Hills, CA
Tour du Mont Blanc
Skye MacDonald was a superb guide. Her cultural, historical, and botanical knowledge is superb! Lynne M., Portola Valley, CA
England Coast to Coast

WT Trip Leader Skye McDonald is coming home to Scotland to lead our new hiking adventure! Check out this video post Skye sent as she scouted the trails and a lovely Georgian-era home that will be our accommodation in Glen Coe—but remember, her scout took place in the wintry days of December. We’ll be there in the long days of summer! Enjoy this peek, and join Skye to hike with us in Scotland!